Acetic Acid → HCID 178506251, compound

HRID 325343Notes

Reaction equation

HRID 325343 reaction equation
Cl[CH2:2][CH:3]([OH:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=2)=[CH:8][CH:7]=1.[OH-].[K+].C(O)(=O)C>CO>[O:21]1[CH2:2][CH:3]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 178520787HCID 178520787, compound

Product 1

HCID 178506251HCID 178506251, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[p-(3-chloro-2-hydroxypropoxy)phenyl]-4-trifluoromethylimidazole (1.92 g.) in methanol (100 ml.) is added crushed potassium hydroxide (1.5 g.). The mixture is stirred 3 hours at room temperature, neutralized with acetic acid and concentrated under reduced pressure (20 mm. Hg.) over steam. The residue is triturated with water (25 ml.), filtered and recrystallized by dissolving in benzene and adding hexane until turbid. A yield of 1.2 g. of 2-[4-(2,3-epoxypropoxy)phenyl]-4-trifluoromethylimidazole is obtained, m.p. 152°-153.5° C.

Workup

  1. concentrationconcentrated under reduced pressure (20 mm. Hg.) over steam
  2. customThe residue is triturated with water (25 ml.)
  3. filtrationfiltered
  4. customrecrystallized
  5. dissolutionby dissolving in benzene
  6. additionadding hexane until turbid

Sources & evidence

ORD record
ord-5983b1182a2447a59e7516473fb4f0a4
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Reaction notes

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